How can you be trained by a dominant woman to be a sissy maid in real life?

Answer 1

Do you mena "how" in the sense of what techniques can be used to do this to someone or "how" in the sense of "how do I go about arranging to get this

If you mean the later, the primary thing you need for this is a willing partner to take you on as their maid. "Domestic service" is frequently combined by couples with other forms of BDSM activity. As with any other fetish activity, there is a wide variety of commitment, from married couples who just talk about it as fantasy in the bedroom to people who publicly live their fetish lifestyle - and their fantasy of being a "sissy maid" - 24/7/365.

To become one, you need merely find a partner who is interested (or at least willing) to dominate you in this way. Personal ads and activity groups are a common way of meeting like-minded fetishists. Professional Dominatrices are a way to indulge in the fetish for brief periods at a price, but remember to first make sure that the activity is not considered prostitution (and therefore illegal) in your locality. (It is legal in many large US cities).

If you are very serious about being a sisy maid as an identity and lifestyle/career, however, training is available from independant professional dominatrices and even a few schools. Search the internet and you will find these schools/programs. But ask a ot of questions on the front end, as this market place has many more pro-dommes who are really just providing short term role-playing for sexual gratification than real maid service and sissifification training.

If by "how" you meant the former - i.e. "how can it be done" then that is a different question.

Knowledge is power and the knowledge the dominant needs here is the intimate knowledge of the ubmissive's mind, especially as concerns his sense of self, his sexual imagination, and his insecurities. A "sissy" is essentially a man who releases himself from pressures of living up to the social and cultural roles of "being a man," by surrendering the traditional prerogatives and symbols of masculinity. All men feel the burden of living up to cultural expectations of masculinity - although they carry it off to varying degrees. To get a man to put down that burden and accept (even embrace) his deepest fears of emasculation by acting them out, the dominant usually uses the the intimate confidence of their relationship to convince him to share his deepest vulnerabilities and then exploits those same vulnerabilities to manipulate his identity and behavior into what they want. A common way to do this is through the eroticization of fear that is S&M fetish play.

Answer #2:

Inadvertently or because you want to be? You should make value judgements of your own based on what you experience in life, and those people you respect and perceive to be getting on with life in a good way.